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Lanostane-Type Saponins from Vitaliana Primuliflora

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Lanostane-Type Saponins from Vitaliana Primuliflora Communication Lanostane-Type Saponins from Vitaliana primuliflora Maciej Włodarczyk 1,*, Antoni Szumny 2 and Michał Gleńsk 1 1 Department of Pharmacognosy and Herbal Medicines, Faculty of Pharmacy with Division of Laboratory Diagnostics, Wroclaw Medical University; Borowska 211a, 50-556 Wroclaw, Poland; [email protected] 2 Department of Chemistry, Faculty of Food Science, Wrocław University of Environmental and Life Sciences; Norwida 25, 50-375 Wroclaw, Poland; [email protected] * Correspondence: [email protected]; Tel.: +48-71-78-40-223 Received: 1 April 2019; Accepted: 22 April 2019; Published: 23 April 2019 Abstract: The phytochemistry of the genera Androsace, Cortusa, Soldanella, and Vitaliana, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana. These two nor- triterpenoid saponins were characterized as (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-β-D- glucopyranosyl-(1→2)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-O-α-L- arabinopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one and (23S)-17α,23- epoxy-29-hydroxy-3β-[(O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-O-α-L- arabinopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-nor-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae. Keywords: Androsace; Douglasia; Primula; Vitaliana; Primulaceae; primrose; triterpenoid saponin; steroid saponins; lanostane; UHPLC screening 1. Introduction Some plants are rich in secondary metabolites of a specific class, e.g., saponins. They can reach up to 10% of dry mass and, thus, are attractive for industrial usage. Among them, steroidal saponins are particularly abundant in monocotyledons, while triterpenoid saponins are abundant in eudicotyledons, with several exceptions. Among a few cases of medicinally valuable steroidal glycosides present in angiosperms, cardiac glycosides and their open-lactone analogs should be mentioned [1]. Other economically important compounds are appetite suppressants from the South African Hoodia sp., Euphorbiaceae [2] or male hormone imitators from Tribulus sp., Zygophyllaceae [3]. On the other hand, typical triterpenoids (C30) are rare in monocotyledons [4]. Taking under consideration the nomenclatural ambiguity of saponins, some researchers classify tetracyclic triterpenoids, for example, ginseng dammaranes, as steroids, and this term regularly appears in some papers [5]. With lanostanes: Some classify them as steroids because of the biosynthesis step of squalene cyclization and mutual conformation of the resulting rings [6–8], while Molecules 2019, 24, 1606; doi:10.3390/molecules24081606 www.mdpi.com/journal/molecules Molecules 2019, 24, 1606 2 of 17 others catalog them as triterpenoids by the presence of two methyl substituents in position 4 and count the total carbon number of this aglycone as 30 [7,9]. Lanostane homologs are uncommon in dicotyledonous plants [7]. They can be found in many Asparagaceae members like in ornamental muscari or squills [10] and conifers [11]. A variety of sea cucumbers should be mentioned as a non-vegetable lanostane source [12,13]. A considerable number of bioactive, non-glycosidic lanostanes was reported in some fungi, including the famous Ganoderma sp. [14,15]. Up to now, the Primulaceae family was known to be a source of triterpenoid saponins of the oleanane type [16] and several cucurbitacins [17], beside several unique flavonoids [18,19]. Performing the phytochemical screening and characterization of this family, we have developed rapid, useful, and universal UHPLC-MS and -MS/MS methods for saponin determination. Moreover, we described the isolation and identification of two dominant saponins from Vitaliana primuliflora Bertol., that were previously observed on thin layer chromatography (TLC) only [20]. Finally, we proved the occurrence of these two 27-nor-lanostane saponins in some species belonging to Androsace (in Aretia and Douglasia sections only). It is also the first communication describing plant nor- lanostanes outside the Asparagaceae family. 2. Results Hydroalcoholic plant extracts were prepared routinely and analyzed by UHPLC-MS and UHPLC-MS/MS in the negative mode as a part of a more comprehensive screening. The first examination of MS chromatograms revealed two main unidentifiable ions of high intensity, especially in Vitaliana species extracts. Later on, about 13 g of underground parts of V. primuliflora subsp. praetutiana were taken for extraction. Subsequently, with the help of semi-preparative flash chromatography on silica and HPLC on reversed phase, we have obtained approximately 40 mg of 12 and 36 mg of 13, as amorphic white solids (almost 0.3% of starting dry mass each; Figure 1). Both compounds could form a stable foam at a concentration of 0.1 mg/mL. The isolation was performed in mild conditions to avoid any artifact formation. All fractionation steps were monitored by TLC/HPLC. 2.1. Structure Elucidation of New Saponins The HRMS spectrum revealed the molecular formula of 12, the most abundant peak (Rt = 13.98 min, UVmax = 199 nm) to be C58H94O27 ([M − H]− = 1221.5910 m/z (calcd.) vs. 1221.5889 m/z (meas.), err. 1.7 ppm). The MS/MS fragmentation indicated the gradual loss of hexose, deoxyhexose, hexose, pentose, and hexose. The lack of coexisting significant fragmentation peaks suggested that the sugars were linearly arranged in one glycone chain. The resulting aglycone was found to have a formula of C29H26O4 ([M − H]− = 457.3323 m/z (calcd.) vs. 457.3310 m/z (meas.), err. 2.9 ppm). Sugar identity (glucose, arabinose, rhamnose) was confirmed after acidic hydrolysis on TLC as described previously [21]. 1H-NMR and heteronuclear single quantum coherence (HSQC) spectrum of 12 showed five anomeric signals. Two of them, observed as narrow doublets, were initially assigned to α-L sugars while three wide doublets were key to β-D sugars [22]. Overlapping 1H signals were resolved by the examination of HSQC and heteronuclear multiple bond correlation (HMBC) together with total correlated spectroscopy (TOCSY) and finally defined by heteronuclear two bond correlation (H2BC). Sugar chain linearity and positions of substitution were confirmed by 2D-NMR as shown in Figure 2a,b. Briefly, anomeric hydrogen of first glucose moiety was HMBC correlated with C3 of the aglycone and HMBC correlation from H3 to C1 of the first glucose was observed. This pointed out the place of substitution of the aglycone with the sugar chain. The C6 signal of the first Glcp was shifted downfield by 6 ppm relative to the non-substituted Glcp. This chemical shift difference suggested Arap was linked to the C6 of the first Glcp. Anomeric hydrogen of the second glucose unit was correlated not only with C2 of arabinose but also with C1 of arabinose. That was the reason the second glucose was linked (1→2) to arabinose. C2 signal of the second glucose was shifted downfield relative to the non-substituted Glcp. That remarked that this sugar was substituted with the next one Molecules 2019, 24, 1606 3 of 17 (rhamnose). HMBC correlations verified that supposition. The observation of highly shifted C2 of Rhap (up to 83 ppm) together with long-range HMBC of an anomeric proton from the third Glcp determined the position of substitution at the end of the sugar chain. The 13C chemical shifts of the glycone part of 12 were strictly similar to those reported in the literature [23–25]. The general pattern of the 13C-NMR spectrum showed similarity of the aglycone of 12 to the well-known eucosterol [25]. Seven methyl groups (two of them split by nodal hydrogen), together with 14 methylene groups and eight quaternary carbons were observed. One of the methyl doublets was ascribed to the sugar unit (Rhap) while the second was ascribed to C21 of eucosterol. The examination of long-range HMBC correlations of the rest of the methyls and of well-separated H3 and H5, let us build a skeleton of the lanosterol-like molecule. Among quaternary carbon signals, the highest shift at 208.6 ppm was assigned to the carbonyl. The two double-bond forming carbons were observed at about 135 ppm (close to pyridine-d5 signals). Spiro carbon was visible at 96.2 ppm. The remaining four quaternary carbons were fixed to aglycone nodes, each substituted with the methyl group. Four methylene groups were assigned to terminal carbons of sugars (3× glucose, 1× arabinose). Another one was assigned to oxygenated methyl (C29, –CH2OH) in the close neighborhood of C5 and methyl C28 (based on HMBC and nuclear Overhauser effect spectroscopy (NOESY)). Compared to eucosterol, C15 of 12 remained unsubstituted (based on TOCSY and HMBC correlations), while the side chain (C24–C26) seemed to be modified. It was observed, that the side chain showed a significant downfield shift of the terminal CH3 group from 7 to 30 ppm compared to reference [25]. Quaternary carbonyl was the nearest neighbor to this CH3 group and two CH2 hydrogens were HMBC correlated both with carbonyl and epoxy ring hydrogens and carbons. Thus the order of =CH2 and =CO in the C24–C26 chain had to be reversed compared to eucosterol. Detailed HMBC, TOCSY, and NOESY examination revealed the rest of well-separated signals typical for eucosterol (Tables 1 and 2).
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